


A Lot to Learn

by Unforth



Series: SPN Kink Bingo 2017 [3]
Category: Supernatural
Genre: Alternate Universe - College/University, Athlete Dean, Bottom Dean, Gay Castiel, Internalized Homophobia, Loss of Virginity, M/M, Nerd Castiel, Openly Bisexual Dean Winchester, Protective Dean, Smart Dean, Top Castiel, Twink Castiel, Virgin Castiel, Wingman Balthazar, Wingman Gabriel
Language: English
Status: Completed
Published: 2017-08-06
Updated: 2017-08-06
Packaged: 2018-12-11 23:46:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,833
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11725095
Author URL: https://archiveofourown.org/users/Unforth/pseuds/Unforth
Summary: Castiel is away at college, and the urging of his friends Balthazar and Gabriel, has gone to the local gay bar in search of a one night stand...instead, he finds his high school crush, Dean Winchester.Written for SPN Kink Bingo 2017, square: Virginity





	A Lot to Learn

**Author's Note:**

> Hey guys! Sorry it's been a little quiet around these parts, I've been in full-on "write DCBB or die" mode because we were required to hit 80% of our estimated word count by check ins on August 3rd, and, as you can guess if you've ever met me, mine is very long and so that was a slog. But the goal is hit and I need a bit of a brain reset so here, have some Kink.
> 
> This story was written for SPN Kink Bingo. You can read more about the challenge [here](http://spnkinkbingo.tumblr.com/about).
> 
> All Kink Bingo entries are cross posted to Tumblr. Feel free to follow me at [unforth-ninawaters](unforth-ninawaters.tumblr.com).

_What am I doing here?_

Shifting, Castiel glanced toward the door of the club. Balthazar and Gabriel were off playing wingmen for him, moving around the crowd with practiced ease, schmoozing about Castiel’s desirable qualities to anyone who would listen. With neither paying attention, surely he could sneak off. The music was overloud, the air stifling, the lights dim, flashes of color catching the facial features of those on the ever-shifting dance floor. Castiel had never danced, had never been to a club, had never been drunk, had never even dated someone. It wasn’t that he didn’t _want_ to – okay, he didn’t want to dance, he didn’t want to be at the club, and if how Balthazar acted when tipsy was what would happen to Castiel, he definitely didn’t want to over-indulge in alcohol – but he _did_ want to date.

Seeking a partner at home would have required coming out of the closet.

There’d been no call to rock the boat. Easier to pretend to be the good little Baptist boy his parents dreamed of raising. Easier to take a vow of chastity. Easier to have a convenient, ready-made excuse to spout every time a girl asked him out, called him cute, suggested that one kiss wouldn’t invalidate his “purity,” as if Castiel actually cared about his purity. He didn’t want to get bullied or ostracized. If not for that...

The only person Castiel had wanted to kiss was Dean Winchester, two years older than him, valedictorian, quarterback, and lady’s man. Dean would _never_ have gone out with a man. At least Castiel had been spared further temptation and guilt when Dean graduated while he was a sophomore.

High school was behind Castiel, and college well underway. Worried that they’d feel he was duping them, he’d come out to Balthazar and Gabriel when they’d asked him to be their roommate sophomore year. Castiel had feared they’d no longer want to room with him. After all, straight men didn’t want to live with _gay men_ , what if it was...contagious? What if he stared at them naked? The thought certainly made _Castiel_ uncomfortable, but Balthazar and Gabriel’s had been surprised that he was concerned. Apparently Balthazar was bisexual, and Gabriel claimed to be something called “pan,” and Castiel felt like an idiot because he’d had no idea what that meant and was too embarrassed to ask.

They’d each propositioned him after that.

At the time, Castiel had declined because they were friends first, soon to be roommates, and he was worried a sexual encounter with either man would result in awkwardness. Finding someone with whom to share a single night had seemed a better plan, to get him past his nerves, to help him get over his internalized idea that there was something wrong with his desires.

_There’s nothing wrong with how I am. The problem is with the society that raised me to feel impure when I’d done nothing wrong._

_By any definition, losing my virginity to a stranger at a bar would count as ‘wrong.’_

_But there’s nothing wrong with the fact that I_ want _to do that, or that I want to be with a man...I’m just violating norms in my means of execution..._

_...not that I’m planning on executing anything...I shouldn’t be here..._

Castiel took a step toward the exit, a second, a third, keeping his back to the wall. The distance between him and escape seemed insurmountable, but if he kept his cool, and if Gabriel and Balthazar didn’t catch him and shame him into staying...

“Hey, Cas,” said a deep, unfamiliar voice. Castiel startled, a hand flying to his suddenly racing heart, and he turned to see who had spoken to him.

Dean.

Winchester.

“Oh my God,” Castiel blurted, then flushed red.

They were at a gay bar!

All the men danced with men!

All the women danced with women!

Castiel was gay, so of _course_ he looked for a hook up here.

Why was _Dean Winchester_ , dean’s list, full athletic scholarship, NCAA all-American, in a gay bar?

“Smooth,” Dean said with a broad smile that crinkled the skin around his eyes and caused the flickering lights to play off his perfect cheekbones. With the gracefulness that only comfort in one’s body and comfort in one’s place in the world could bring, Dean slid beside him, leaning casually against the wall. Castiel looked like he was hiding, cowering like a wallflower; Dean effortlessly made nearly identical movements seem suave, thought out, and hip.

_Is...is hip a thing people still say? How am I supposed to know, I’m about as far from hip as it’s possible to be! Oh God, why is he even talking to me?_

“Did you know there are these two guys moving ‘round the dance floor, telling every dude in earshot that they’ve got a virgin twink they want to get laid?” said Dean. Someone approached them from out of the darkness, a smile on his face, only to blanch and fade back into the crowd at a glare from Dean.

“That’s...that’s really what they’re saying about me?” Castiel asked, feeling sick.

“They’re _slightly_ less overt and offensive about it, but basically, yeah – doesn’t take a rocket scientist to read between the lines,” Dean conceded.

“I need to get out of here,” said Castiel, taking a more decisive step toward the door.

“That’s what I came over to check,” confirmed Dean. “Honestly when they said ‘Cas’ and pointed toward the wall I thought it couldn’t be the same nerdy Jesus-y dude I knew in high school but it worried me enough that I figured it was no skin off my teeth to check. Your friends – I think their hearts are in the right place – smack dab in the middle of their chests – but you should maybe have a talk with them about approach.”

“No...” said Castiel vaguely, weaving between oblivious people in an effort to escape to the fresh air outdoors. Dean trailed him, a reassuring shadow, and though Castiel couldn’t see Dean’s face he could imagine the glare that drove away everyone who tried to approach Castiel. “I mean...we talked about this...I agreed...they’re only saying what I wanted.”

“Really?” Dean asked skeptically.

“Lookin’ for a top, little twink?” leered a stranger from the crowd. Terrified for no reason he could identify, Castiel froze. A possessive hand closed around Castiel’s shoulder, Dean stepped up beside him, and Castiel looked at him gratefully. “Never mind,” grumbled the man, “guess this ride’s taken.”

“Top?” asked Castiel, heaving a relieved sigh. “Ride?”

“He wanted to fuck you in the ass, Cas,” Dean explained. “You expect me to believe those two friends of yours were looking out for you when they let you loose on this place without even explaining to you about topping and bottoming?”

Castiel’s stomach flipped. “No – I mean, I know about – I didn’t think through...I’m sorry. I have to get out of here.”

With a grunt, Dean stepped up in front of him, broad shoulders made more pronounced by a subtle shift in how he held himself, and with the expertise of a linebacker Dean forged a path directly to the door. Castiel kept a hand on the loose fabric at the back of Dean’s shirt and allowed himself to be pulled in Dean’s wake. A shove popped the door open abruptly enough to prompt a squawk from someone on the other side, and then they were outside, they were free, and air inundated Castiel’s reeling senses. Head spinning, he fell against the wall next to the door, hands on his knees, eyes fixed on the ground, stomach flipping.

“Ew, gross, don’t ralph on the shoes!”

There were still people around, a cloud of stale cigarette smoke making a miasma that clogged Castiel’s nose, and he didn’t know who’d spoken. Dean seemed to have vanished and Castiel struggled to gather himself. Relying on Dean was absurd. They’d not seen each other in two years and had barely been acquaintances in high school. Heck, it was miracle Dean even knew who Castiel was, knew his name, knew about his chastity pledge. Their relationship was nonexistent; for Castiel to rely on him now...

“Woah, buddy, you okay?” Dean materialized in front of him, blocking the glare of a nearby streetlight. “Someone give you booze?”

“No...” Castiel grabbed at his wristband, identifying him as a minor who’d paid the cover charge. “I’m sorry.”

“Don’t apologize. Look, how about I give you a ride home?”

“Why were you at the bar, Dean?” Castiel looked up and met Dean’s shadowed eyes. The streetlight made a halo of Dean’s sun-bleached hair, cast his face into darkness.

“Huh?”

Castiel shook his head, shook off his disorientation. “It’s a _gay bar_. Why are you here?”

“Because I’m bi,” Dean said, puzzled. “And I was looking for a hook up. What’s it matter? It’s no biggie, and you need the help more than I need to get laid.”

_Dean’s bi._

Shock froze Castiel’s features.

_Dean is...Dean isn’t straight..._

“Wait, you didn’t know?” exclaimed Dean. “Dude, I was out in high school!”

“You were?” asked Castiel weakly.

“Yeah, it was _escandalo_ , I even asked Benny to prom! How’d you _not_ know that?”

_How did I not know that?_

_Dean was out in high school, and still popular. Could I...could I have come out? Would that have been okay? I never even thought to ask if there were any gay kids at school..._

_It’s too late to worry about that. Focus on now._

_Dean is...Dean’s available._

_Dean was at the bar, looking for someone to have sex with._

_I was at the bar, looking for someone to have sex with._

Urgency seized Castiel. Grabbing at the front of Dean’s shirt, he crashed their mouths together. Someone standing nearby whooped.

_First kiss...first kiss...it kind of sucks, I don’t feel anything, he’s not kissing me back—_

Dean’s hand on Castiel’s chest shoved him back against the wall. “Woah there,” said Dean. “Communication. What the fuck was that, Cas?”

“Dean – take me home,” Castiel demanded. Dean blinked. “I _did_ come here to lose my virginity. And I chickened out. But...but you’re here. Take me home.” Dean’s eyes went wide and Castiel’s brief burst of confidence crumbled. “I mean. If you want.”

“I want,” Dean breathed, leaning forward, laying a hand on the wall beside Castiel’s head, bringing their faces so close that Castiel thought he could taste him. “Thought about asking _you_ to prom, thought you might be...but you weren’t out, everyone seemed to think you were straight or married to the Holy Trinity or some shit, and I wasn’t about to out you just cause I thought you were adorable...”

“You thought I was adorable?”

“You _are_ ,” said Dean. “And your eyes were always on me...whenever I looked at you, you were lookin’ my way...and looked like...you really want me to...ya know, sex...you’d do that with me?”

“Yes.”

There wasn’t the least doubt in Castiel’s mind.

_I can’t believe I was prepared to make love to a stranger when Dean has been interested in me as long as I’ve been interested in him..._

_...I mean, we barely know each other, it’s just animal attraction...magnetism...lust is one of the seven deadly sins..._

_I’m so ready to be a sinner...and if the goal is to have sex, what do we need other than lust?_

_...and a condom..._

Dean gave him a wobbly, shy, sweet smile, and Castiel’s heart leapt in his chest.

“Take me home, Dean. Now.”

“Yes, sir,” Dean breathed. A shiver trailed through Castiel.

_This has got to be a dream. I got so mixed up at the club that I’m hallucinating._

_I don’t care. If it’s a dream, call me Mr. Sandman._

_Call me ‘sir.’_

* * *

Castiel had always thought Dean was gorgeous. Whether he was in beat up jeans in a t-shirt, sprawled in a desk in class, or fresh off the football field in his uniform, hair matted down from sweat and a victorious grin lightening his features, Dean was flawless in Castiel’s eyes, but now...

Dean lay, naked, on Castiel’s bed. There was a sock on the doorknob to warn Castiel’s roommate away, the bolt secured to guarantee no intrusion. The only part of Dean that wasn’t tanned a stunning golden brown and spattered with freckles was his behind and crotch, both pale around the lines of a speedo.

 _He’d be gorgeous in a speedo, too_.

_He’d be gorgeous in a potato sack._

The thoughts were idle distractions, Castiel’s vain attempt to keep a hold on himself. Dean was _naked_ , on his _bed_ , in his _room_. Dean had undone the buttons on Castiel’s shirt, deftly removed Castiel’s belt, shoved down Castiel’s pants, watched as Castiel had finished undressing. Castiel had been unable to keep himself from staring at Dean’s cock. He’d not seen a naked man in...well, basically ever, since early childhood didn’t really count...and while once he’d been worried that his belief he was attracted to men rather than women would evaporate when confronted by an actual man actually interested in him, Castiel no longer worried. He wanted Dean like he wanted air. Need burned in his gut. Dean’s dick was intriguing, a little smaller than Castiel’s cock and fully erect. When Castiel pulled down his pants and his erection popped free, Dean’s dick had bobbed and a bead of thin liquid at formed at the tip.

_I want this._

_And he wants this._

_That’s...that’s incredible..._

“I’m ready,” Dean breathed, rolling onto his belly and spreading his legs.

Dean had produced a condom and rolled it down the length of Castiel’s cock, staring into Castiel’s eyes the whole time.

Dean had _gone to the club wearing a butt plug_.

Castiel had assumed that Dean would want to fuck him, or trade blow jobs, or something, and any of those options had appealed to him, but this...if Castiel could have described his perfect scenario for his first time, it would have closely resembled the supposed reality unfolding around him.

_Supposed reality...oh yeah, ‘cause definitely a dream..._

_...does that mean he’d call me ‘sir’ again, if I asked?_

_Better not to push it...he’s already doing so much for me...putting up with so much from me...it’d be a shame if I woke up now..._

Heart thrumming with nerves, Castiel climbed onto the bed and positioned himself where he thought he should be. His cock bobbed in the air over Dean’s crack, lubricant smeared thick around the black plug glistening in the lamp light.

“What do I...what do I do?” asked Castiel hoarsely.

“Pull the plug out – _gently_ ,” Dean instructed. Castiel obeyed, twisting the sex toy around before he carefully withdrew it. Dean leaked a beautiful noise and Castiel’s chest clenched. He was nervous and excited and terrified and God, he wanted to do a good job, he wanted to please Dean – what if he screwed up? What if he came too quickly? Maybe he should have gotten some practice before hooking up with his dream guy. It was too late now, though. _Maybe he’ll let me practice on him, in the future, again and again...I have to do well!_

“Use one of your hands to line your dick up with my hole and get yourself started, then lie down over me to...you know...”

“Okay...” The word came out as a near-silent rasp. Castiel licked his lips, set the plug aside, and stared down at the vision before him. A thick bead of lube leaked down Dean’s perineum, his pucker stretched, skin pale around a dark opening.

_He wants me inside him._

“This okay, Cas?”

_Oh, hell._

“This is...this is so much better than okay,” Castiel managed.

_No point putting it off..._

With a heartening breath, Castiel did as Dean suggested, lined himself up and pressed the tip of his rubber-covered cock against Dean’s hole. Incredible heat teased at him and Castiel couldn’t stop a frantic whimper; he leaned forward and pressed into Dean’s body, easily sliding in until his hips rested flush atop Dean’s shapely ass.

“Fuck,” Dean groaned. “Fuck that’s...”

“Are you alright?” asked Castiel. A strained note in Dean’s voice alarmed Castiel, and only his concern kept his instincts at bay. His body screamed that he had to heft himself up and thrust back down, had to chase the orgasm already boiling beneath his skin. Dean was hot and tight and slick and good, so _incredibly_ good. Everyone had told Castiel sex was spectacular but the things they’d described doing with women had never appealed to him, so he’d wondered...but no, this was every bit as good as he’d been led to believe. This was _better_.

_I’m...I’m going to fuck Dean Wincester..._

He giggled.

“Are _you_ alright?” Dean countered.

“I’m _awesome_.”

“Okay...okay, cowboy, just hold your horses a minute, okay? I’ve never...” Dean shimmied beneath him and light like starbursts blanked the room.

 _He’s never_ what _? Bottomed? He was wearing a plug! He must have..._

“...I mean, I saw that you were big, but hot _damn_ , dude, how’d you keep that thing in your pants all these years?”

“Dean...” Castiel panted. Dean was a solid, muscular weight beneath him, around him, and the longer they delayed the more difficult it grew for Castiel to restrain himself. “Wait...I’m...are you saying I’m well-endowed?”

“‘Well-endowed,’” Dean mimicked. “Cas, you’re hung like a fuckin’ horse. How’d you _not_ know that?”

“I’ve had no basis for comparison...”

“ _None_? Locker rooms? Roommate? Siblings? Porn? _Nothing_?”

“No,” said Castiel, stunned. “Is...is this a good thing?”

“Might not be everyone’s cup of tea but as far as I’m concerned? Sign me the fuck up.” Dean’s approval cast warmth through Castiel. Desperate for _any_ contact, he tentatively placed a kiss on the curve of Dean’s neck. Dean shuddered, shook around him, and Castiel moaned. “So, now that you’re in me, and I’m as ready as I’m gonna be, what ya gotta do is—”

Castiel lifted his hips and slammed them back down. Euphoric pleasure exploded outward from his dick, enveloping him, and Dean cried out. A glimmer of concern trailed through Castiel but now that he was moving, there was no stopping. He drew his hips back again, pulled himself mostly out of Dean’s body, and thrust in again hard, not pausing as he did it again, again, again. Dean made no protest, only moaned and gasped and shimmied back against him. Dean was bigger than Castiel, stronger than Castiel, but in this position Castiel felt _powerful_ : Dean pinned beneath him, held down by Castiel’s full bodyweight, his body _spitted_ on Castiel’s cock.

_I. am. in. Dean. Winchester._

“Oh, God,” he groaned.

“Yeah – yeah it’s good, don’t stop, don’t stop,” Dean panted.

As if Castiel could _possibly_ stop.

Frantic, Castiel drove into the heat and wetness beneath him, mouthed at Dean’s skin, fingers digging into Dean’s shoulders. Every sound Dean made spurred Castiel to thrust harder, the muscles of his thighs burning with the effort, and it was all Castiel could do to ride the bliss inundating him and try not to incinerate. Dean bucked back against him with a desperate noise, lifting his hips, fumbling a hand beneath himself. The tightness around Castiel clenched and his tenuous hold on self-control evaporated. With a guttural groan, hips stuttering erratically, Castiel filled the condom.

With a gulping gasp, he collapsed atop Dean, who grunted and groaned.

“ ‘m sorry,” Castiel managed. “Sorry...”

_At least I lasted a long time, I..._

His eye caught the clock beside the bed.

Those were the longest three minutes of Castiel’s life.

“Sorry, Dean,” he groaned, mortified.

“Don’t be,” murmured Dean. “I’m good.”

“You achieved an orgasm?”

Dean snorted. “Yeah, Cas, I came. Spurted all over your bed. Happy?”

“Very,” said Castiel sincerely. His hips shifted against Dean’s ass, his cock twitched, and he moaned as a wave of pleasure shocked through him, so intense it was painful. “Can we...can we do that again sometime?”

“Dude, wow – just got your rocks off and you’re _already_ thinkin’ ‘bout more? And here I thought _I_ had a crazy recovery time...”

“No...I mean...that was great, I...” Castiel flushed and rolled off Dean’s back, slamming into the wall beside the narrow bed. Two near-grown men was a tight fit in a twin. _Maybe Dean’s got a larger bed wherever he lives?_ Dean twisted to look at him, cheeks flushed and sweaty, a dopey smile bringing a lovely glimmer to his eyes. “I’ve heard terms...‘one night stand’ and ‘walk of shame’ and...and I’ve liked you for a long time, Dean. I’d prefer you not leave right away, and I was worried. I don’t understand the standard etiquette at a moment such as this. I’d like to...but it’s up to you.”

“You... _you_ liked _me_?” asked Dean incredulously. Castiel nodded. “Hell, shoulda asked you to prom after all.”

“Better late than never?” Castiel replied, hope sparking in his chest.

“Fuck no, not asking you to prom _now_ ,” said Dean, rolling his eyes. The hope flickered out, disappointment causing Castiel to slump against the bed. Dean laughed. “You, me, date, Mama Bear’s Pizza, tomorrow at 8?”

Castiel’s jaw dropped. “ _Really_?”

“Really,” Dean grinned, then winked. “‘Cause that was good and all – but dude, you’re _such_ a virgin. You have got a _lot_ to learn about how to satisfy a dude.”

“And you want to teach me?”

“I literally cannot think of a better way to use my time.”

Dean sounded utterly sincere.

“8 tomorrow,” Castiel confirmed, grinning. “And Dean...?”

“Ask me anything,” Dean said, rolling onto his side and sweeping his arm in a magnanimous gesture. “Doctor Sexy is _in_ for all your sex-related queries.”

“Maybe...maybe, sometime, you could call me ‘sir’ again?”

Dean blinked, and his lips cracked into his widest smile yet.

“Fuck, Cas...yeah, we’re gonna get along _just_ fine...the shit I can teach you...”

“I can’t wait,” said Castiel. Leaning toward Dean, he brought their lips together. Dean’s mouth was soft beneath his, lips working, and though Castiel felt clumsy and inept, the kiss still felt good.

_So much to learn...but he’ll teach me..._

The evening hadn’t gone _quite_ as Balthazar and Gabriel had intended...but something told Castiel his friends wouldn’t mind that he’d ditched them and made a match on his own.

_Me and Dean Winchester?_

_Assuming I never wake up from this..._

_I’ll have to buy those two a damn fruit basket or something...or, like, beer. They’d probably prefer beer. Dean is 21...I could ask him to pick out something appropriate..._

“I can’t wait,” Castiel murmured again. Meeting Dean’s eyes, he let his thoughts slip into happy fantasies.

_Tonight is the first night of the rest of my life..._

_...I can’t wait to learn everything he can teach me..._

_...and maybe teach him a thing or two, as well._

**Author's Note:**

>  **End note cross posted from "Dads to Be" and "Two Can Play at The Game."**. If you read it there, please skip, but if you didn't...
> 
> Alright, guys, as an end note...of late there's been a big trend of people in comments asking me to continue my ficlets or expand them into 'verses. Getting inundated with comments like that has been causing me a LOT of stress, has led to me not wanting to write short stories, and has also resulted in me not checking my comments and falling way behind in replying because every time I see it, it _hurts_.
> 
> I appreciate the compliment paid when someone says, "you wrote this short thing and it's great and I want more!" That's a kind sentiment, but please consider the implications. I have written about a hundred shorts and many longer stories, several of which are popular and still works in progress. When one person says, "please expand this story!" it's pleasant but when ten people say it on every story, AND I'm getting asked to continue my works in progress, AND I'm getting asked for time stamps and sequels, it goes from seeming like a compliment and being nice to being utterly overwhelming. Please remember that I see your single comment in the context of everyone else's, not in a void where no one else has ever asked me for a sequel.
> 
> I work a full time job.
> 
> I have written an average of 2500 words per day since January 1st, and have also edited an average of 9 pages per day since January 1st.
> 
> During the day I watch my 17 month old son for up to ten hours while my wife is at work, with my own full time job jigsawed around that.
> 
> I am currently 8 weeks pregnant.
> 
> When I say I can't do more, I mean that entirely literally. I already don't have enough time for myself. It is impossible for me to turn every story into a 'verse, and I do receive requests on virtually every story. While I understand objectively that this is meant as a kindness, with the volume of such comments I've received it's come to feel like a demand, and an unappreciative one at that.
> 
> So consider this my universal request: _please_ stop asking me to continue stories in your comments.
> 
> If you really want me to follow up on a specific 'verse, please save your request for when I next put out a [Call for Prompts](http://archiveofourown.org/works/11408007). Until then...just stop. I can't deal with it. I will stop writing shorts if people keep doing this, because it's causing me so much stress. Seriously I'm starting to dread the flood of "omg write more!" that I get every time, to the point that it's making me not want to write. Since I know that's no one's goal with those kinds of comments...
> 
> ...yeah, just don't. I honestly don't know a single author who appreciates these kinds of comments. We talk about it a lot on Tumblr but I realize a lot of you aren't on Tumblr so consider this me spreading the word: this kind of comment really comes off as pressuring and inconsiderate to authors.
> 
> I will be cross posting this author's note over my next few stories, to spread the word. Thanks for your time and consideration, guys.
> 
> (and if you leave this kind of comment going forward I will direct you to read the author's note and otherwise not reply.)


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